Young Love and Missing Cats
by Infrared-Ultraviolet
Summary: Anna has had a crush on her neighbor Hiccup Haddock for years, but she doesn't think he'll ever notice her. However, when Hiccup's beloved cat Toothless goes missing and Anna knows just how to find him, she might finally have her chance! Modern AU Hiccanna.
**Disclaimer: I DO NOT OWN THE PREVIEW PICTURE! IT BELONGS TO AlexDasMaster ON DEVIANTART! I also do not own any of the characters. All I own is the storyline.**

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It so happened that that particular Thursday Anna finished her homework earlier than she thought she would, and was able to set aside an hour to listen to her playlist while gazing longingly out her front window.

It was a playlist she had spent days making, finding only the best Taylor Swift songs to describe her massive crush on Hiccup Haddock. Anna didn't much like her newer songs, singing of passionate, brief love affairs which were gone too soon. No, she much preferred the older songs in which Taylor sang wistfully about unrequited feelings for boys who weren't aware of her existence. That was certainly something Anna could relate to.

As she put her headphones in and looked out at Hiccup's house across the street, she let out an annoyed huff. She couldn't deny that the whole thing felt a little unfair sometimes. It felt like everyone around her but her was finding love. Her best friend Rapunzel had finally asked out her crush since kindergarten, Jack Overland-Frost, in their freshman year, and the two had been happily dating ever since. Even her sister Elsa, never much the romantic type, had managed to pick up a suave and charming boyfriend by the name of Flynn Rider at college. And here Anna was, still pining over the same boy she'd been pining over for years and years, unable to have an intelligible conversation with him without making a complete fool of herself.

He hadn't grown into the type of boy most girls Anna's age would have preferred. He hadn't even been a particularly attractive kid, with his "scrawny limbs and ridiculous bowl haircut," as Elsa always said. But Anna was hardly into him for his looks. What she had fallen for was the way he once made his front yard into a fantasy world, perching his stuffed and plastic dragons in trees and bushes and taking turns flying them down the sidewalk, making dramatic _whoosh_ sound effects as he went. What she had fallen for was how he had never really stopped living in his fantasy worlds, always reading the nerdiest novels on the planet (usually novelizations of video games) on his front porch as he got older, all the while grinning like an idiot. And when the brunette boy wasn't reading, he was scribbling furiously in a sketchbook, drawing the imaginary realms that made him so absolutely fascinating.

So of course Anna's attraction to her neighbor was far from hormone-driven, but that didn't make it any easier to interact with him. It felt like every time she tried to talk to him at school, something stupid slipped out and her entire being seared with the worst kind of awkwardness. It didn't much help that he usually said something sarcastic to diffuse the tension, and oftentimes she couldn't tell if he was joking or not.

Taylor was busy singing about wanting some guy to notice her while he was in love with another uninterested girl (which was true in Anna and Hiccup's case to some extent, seeing as she always caught him ogling Astrid Hofferson in class. Not like Anna had ever felt particularly threatened by the situation since she knew it was only a matter of time before Hiccup figured out that Astrid was, in fact, a lesbian, and was, in fact, dating Merida Dunbroch) when Hiccup emerged from his front door. From the look on his face, he seemed to be rather upset. He paced up and down his yard, yelling something over and over. He set off down the sidewalk, still yelling. Anna paused her music and put her iPod down.

She was just about to open her front door to determine what he was yelling about when it occurred to her that she had to look presentable. She rushed into her room and shed her sweatpants, replacing them with a pair of jeans. She pulled her cutest pink sweater over her baggy t-shirt, hoping the two items of clothing didn't clash too badly.

As she slipped outside, Anna came to the realization that what Hiccup was yelling over and over was his cat's name. By the time she got outside, he was making his way back toward his yard, still shouting "Toothless!" over and over. Seeming to finally give up, he slumped down on his porch, looking quite despondent.

Anna fidgeted anxiously, unsure of whether to make a dash across the street and ask Hiccup if he was all right or slink back into the safety of her house before he looked up and saw her just kind of awkwardly standing there. The former option definitely sounded better, but it required a courage that Anna wasn't sure she had.

She stood on her porch for several seconds, glancing uneasily from her neighbor to her front door and back again. _I want to go talk to him, but…what if he thinks I'm a freak for asking if he's okay? What if he's like, "Oh, she's barely talked to me for 11 years, why does she suddenly care about my well-being?" What if he gives me a confused and slightly disgusted look and there's this long awkward silence? What if I trip and fall on my face? What if he says, "Like I would tell you, you weirdo! Go back to being antisocial!" and then laughs at me?_

She cast another look at Hiccup. He looked truly defeated, sitting on his porch with his head in his hands, and he looked very much like he needed a neighbor to comfort him. Anna took a deep breath. _Okay, fifteen seconds. I just need to be brave for fifteen seconds. Enough time to cross the street._

Face hard with determination, she tromped down the sidewalk and marched across the road. Head held high and lungs puffed out, Anna was too busy radiating false confidence to notice the curb fast approaching her foot. It caught her toe at just the wrong moment, and before she could even let out a squeak of alarm she was sailing through the air, receiving a mouthful of the grass of Hiccup's front yard a few moments later.

"Uh…are you okay?"

Anna rolled over to see Hiccup Haddock looking down at her. He looked concerned, but she could tell he was holding back a smirk. The corners of his mouth were tugging at his expression the way they always did when he was trying not to laugh.

"Oh, yeah, I'm totally, completely fine!" Anna replied quickly, laughing nervously. "I was actually coming over here to ask if _you_ were okay. I heard you calling your cat, and now you seem really upset."

Whatever hint of a smile there was on his face disappeared. "Yeah, Toothless slipped out of the house earlier, and now I can't find him anywhere. I'm just really concerned because he's declawed, you know? If anything attacks him out there, the poor guy can't do much to save himself."

Anna nodded, wriggling up into a sitting position and regarding the boy sympathetically. So of course her crush would be worried. He always spoke so fondly of Toothless, and she could only imagine how upset he would be if the frisky black cat got lost or hurt.

But as she studied the downtrodden brunette, she found that the gears in her brain were beginning to turn, and a helpful memory from 6 years prior suddenly surfaced.

"I can find Toothless!" she blurted out.

This revelation seemed to surprise Hiccup quite a bit. "Really?" he asked.

"Yeah!" Anna replied, breaking into a grin. "They taught us all about animal-tracking at Girl Scout camp. I was…always sorta good at it." She pushed a strand of hair bashfully behind her ear before continuing. "I've never tried it in the city before, but I'm going to give it a shot and see if I can find Toothless!"

"You…you really think you can find him?" Hiccup's dark green eyes glimmered hopefully.

"I can sure try!" Anna giggled. A thought suddenly occurred to her, and she looked back over at her house. "Okay, just wait right there for a sec."

Anna rushed back over to her house and emerged a couple minutes later holding a half-opened can of tuna and a hefty softball bat. Hiccup looked more than suspicious.

"Er…Anna? What's the huge bat for?"

She grinned proudly. "Well, you said Toothless is declawed, so I'm bringing this along in case I find any mean stray animals giving him trouble when I find him!"

To Anna's delight, Hiccup's surprised look quickly turned to an impressed one. He nodded encouragingly.

"Well, all right then. Looks like you're all set."

"You'd better believe it!" Anna replied, grinning. "Now you can keep looking around the block, and I'm going to go check if he went any farther."

"Ah…thanks!" Hiccup offered her a small smile, and Anna's entire heart melted into non-functioning goop. "You know, I really appreciate you offering to find Toothless for me. I'm going to be in you debt forever if you do."

"R—really?" Anna's cheeks turned bright red. "Uhhhh…don't mention it! I'm actually super bored anyway, and this'll be a great adventure! Heh."

She gazed at him for a few seconds, lovestruck grin adorning her face. She only noticed she had been looking too long when he began to fidget uncomfortably.

"Well, I guess I should be off, then!" she said quickly. "Can't waste any time if Toothless might be in trouble. Don't worry Hiccup, I'll find him for ya!" she called over her shoulder as she raced down the block.

She slowed from a sprint to a jog once she was a few houses away, trying to gather her thoughts. _Now let's see…where would I go first if I was a cat?_

Anna didn't need to consider the question long before her eyes fell on a familiar lavender house and the answer became obvious.

Old Sue was known for her soft spot for stray dogs, and often put leftover meat scraps in containers behind her house for them to snack on. However, she was also an adamant pescetarian, which meant the meat containers were usually heavy with the stink of fish and drew in plenty of seafood-loving felines when there didn't happen to be any dogs around. The only person more notorious for leaving leftover food out was Cally, the owner of a pizza parlor a few blocks away. A crazy cat lady in the making, Cally always made a point of looking out for stray cats by providing them with container upon container of leftover anchovies (which, not surprisingly, no one ever ordered on their pizza).

Anna had no idea whether Toothless had made a beeline for the fish house, but it seemed like a good place to start. And given that concrete wasn't a great place to try to find pawmarks, it was the only lead she had.

To Anna's relief, Sue's car was gone, meaning she wouldn't look out her front window and think it was odd that a teenage girl with a softball bat was poking around in her yard. Glancing around to check for witnesses, she decided the coast was clear and made her way down Sue's driveway. The scent of fermenting salmon led her straight to a Tupperware container nestled beside the side porch, half-eaten fish fillet baking in the sunlight.

Anna gagged, half tempted by the scent alone to start her search for clues elsewhere _. No,_ she could practically hear her old counselor Cynthia saying. _There's important information here. Find it, and don't give up so easily!_

Holding her nose, she leaned down to examine the salmon. It was half gone, and the cut down the middle was jagged, not straight like a knife would make, so some animal had definitely been here since Sue had had her lunch 3 hours ago. And a dog would have eaten the whole thing, so it had to have been a cat. And, given that Sue's cat Flopsy was a strictly indoor cat, it had to have been another cat.

Anna let out a squeal of excitement. So a cat _had_ come by here! Whether it was Toothless was entirely up for debate, though. So what else had Cynthia said to look for? Scat, fur, clawmarks…

She scanned the area around the salmon to see if Toothless had left any evidence behind. Before too long, something black caught in Sue's wooden fence caught her attention. On closer inspection, she realized it was a clump of soft, wispy black fur.

She snatched it up and ran it between her fingers. Yep, definitely cat fur. But it could be any old black cat's fur, and there was only one way to find out if it was Toothless's…

She drew it up to her nose and gave it a sniff. It didn't smell like much of anything, but…she did pick up the faintest trace of Hiccup's hoodie-scent. Which she certainly did _not_ recognize because she had leaned over and taken a whiff of his hoodie when he went to go to the bathroom that one time they were seated next to each other in chemistry lab. No, that most certainly did _not_ occur and she really had no idea how she knew what Hiccup's article of clothing smelled like. But nevertheless, the familiar smell only confirmed her suspicions that Toothless had indeed been around here. And judging by the fact the fur was caught in the fence, he had probably jumped over it and gotten his fur caught along the way.

 _Perfect! I'll look for tracks on the other side!_ Anna hurried back up Sue's driveway and down the other side of the wooden fence. The people whose yard this was only lived in the little house during the summer, so once again she had the good fortune of not having to evade the notice of suspicious neighbors who would think to themselves _why is the awkward redhead from across the street crouching down on my grass with her head turned sideways?_

The answer was that Anna was looking for any sign of cat tracks, which were much more difficult to pick up on grass than on dirt. It took a long while of scanning the Wilsons' neatly-groomed grass to pick up on the tiny, almost imperceptible, indents. She had to use a trick a counselor named Halley had taught her, where if the shiny underside of the grass was turned up in a compression, it meant an animal had been there. And luckily, they were spaced diagonally, just like a cat's would be.

 _Wow, I can't believe I remember this much,_ Anna thought gleefully. _And here Elsa was, thinking all Girl Scout camp was ever going to do was make me fat off of cookies!_ Although to be fair, Anna herself had never dreamed that one day she would be using wilderness skills to woo Hiccup Haddock.

She crept through the Wilsons' yard, following the faint tracks. They seemed to be leading right to the road, across which was…the park! Anna let out a delighted squeak, the pieces of the puzzle coming together fluidly in her mind. Of course Toothless went to the park! It would be worlds more interesting to a curious cat than any run-of-the-mill suburban house. There were squirrels to chase, plants to sniff, and an entire gravel playground to poop in.

Anna was so jazzed that she didn't look both ways before crossing the street, and had to jump back just in time as a sports car zoomed by. Stopping to catch her breath, her excitement quickly returned and she bounded across the street and into the little park.

It was a little harder to pick up a trail in the park, seeing as the grass was longer and there was a _lot more of it._ Anna wandered down the main path in frustration, scanning the green stalks for the slightest bit of indent or shininess. _Oh, what's the use?_ she thought, after a long period of frustrated looking. _He could've gone anywhere in this stupid park!_

She was becoming quite discouraged when she caught sight on something small and brown under a tree close to the playground. Upon closer inspection, it was a cluster of neat brown tubes, pushed into a tidy pile and left to warm in the spring sun. Anna didn't think she'd ever been so happy to see cat poop.

No longer caring what passersby thought of her, she crouched down and tilted her head to the side, searching the grass madly. After a couple minutes of looking, she made out the shininess of upturned stalks. Certainly not easy to see, but enough to make out that Toothless was heading straight for the playground.

And where would a cat go on a playground? Anna knew just the place.

Not even bothering to check the gravel for tracks, Anna hopped onto the thick wooden railing that bordered the playground and balanced on it, skirting the edge of it until she reached the sandbox. What better place for a cat to go than a place that reminded him of his familiar litterbox? Anna was rewarded for her troubles with several pawprints—fresh, clear, and _actually resembling paws_ this time—and another pile of cat manure. It glinted slightly in the sun, as the counselor Audrey had always said the fresh scat did—and that was enough proof for Anna that it was from Toothless. She had little intention of leaning down and poking it to make sure it was recent.

Luckily the grass around the playground was sparser, leaving more dirt for a cat to make prints in. Anna found a trail pointing right toward the creek, and without hesitation she bounded over to the little trickle of water. She supposed Toothless could've veered off in the grass between the creek and the playground and gone somewhere else, but she doubted it. It only made sense that after a long 45-ish minutes of eating and pooping and adventuring in the sun, the poor cat would be a bit parched.

At first, the creek didn't seem to bear much evidence that a cat had ever been there. Anna stepped down onto a flat rock sticking out into the current, likely what Toothless had stood on to get a drink. She looked around, letting out a huff of frustration. Had it really been this rock he stood on? Or one farther downstream? The thought of trying to find tracks in the grass again made her head hurt.

Her first reaction to seeing an enormous clump of black fur caught on a stick bobbing in the current was relief. Ah, so Toothless _had_ been over here! But…why was his fur stuck on something so far from the rock? The bank over there was certainly too steep for a cat to drink from. It was almost as if he had brushed past the stick while in the water and a sharp part tore a wad of fur off.

Wait… _in the water?_

Anna bit her lip. _He must've fallen in!_

The realization was so alarming that Anna started, causing her sandaled foot to slip on a wet part of the rock and send her stumbling down into the creek, soaking the bottom of her jeans and giving the rest of her a good splashing. Letting out a grunt, she sloshed through the water and clambered out on the opposite side, setting off at a sprint down the stream bank. All sorts of awful things that she didn't want to think about could happen to Toothless if she didn't catch up to the floating cat in time. He could drown, or hit his head on something, or get stuck under some rock and have water shoved down his throat until he suffocated, or get eaten by a giant crawdad…

Anna was almost at the edge of the park, still with no sighting of Toothless being swept downstream, when she encountered an unexpectedly-soaked patched of grass. With a yelp, she ungracefully toppled over and landed heavily on the park's outer sidewalk, just barely managing to shoot her hands out and stop her head from hitting the pavement.

She sat up and nursed her scraped hands, wincing in pain. As she was brushing the dirt out of the cuts, she noticed a trail of unmistakable, wet pawprints leading away from the patch of grass she had slipped on. Her stomach dropped with relief, and she let out a giddy giggle. _He got out!_

Following the wet pawprints was easy going, and Anna was absolutely elated to have a break. She trotted confidently down the sidewalk, trailing the pawmarks for an entire block and on to the next one. Even when they began to fade, a rotating sprinkler did her the favor of leaving a damp patch on the sidewalk and getting Toothless's paws wet once again. She only encountered trouble once, in the form of an elderly woman weeding her garden eyeing her softball bat judgmentally and asking just where she thought she was going with that big, dangerous thing. To this Anna wildly improvised that she was going to the regional softball championships taking place at the nearby YMCA, and that this was by far the biggest gameday of her life. The old lady didn't seem impressed, but she at least appeared to buy the story, returning to her weeding with only a mutter of "Well, try not to knock someone's head off."

By the time the tracks began to fade again, Anna had left the residential quarter and was nearing Sycamore Shopping Center. A familiar scent drifted to her on the breeze, and her mouth watered. Even from here she could smell Cally's Pizza, situated right across the street from the shopping center. Nothing sounded more delicious at the moment than a nice stuffed-crust after a long, tiring 45 minutes of cat searching.

 _Wait…_ Anna stopped in her tracks, eyes widening in realization. _Cally's!_ If she could smell the food from here, than someone else could as well…

She broke into a sprint toward the stoplight, veering into the alleyway that led behind Cally's. The sound of yowls and spits as she approached the back of the pizza parlor made her double her pace. Upon spotting a hazy black shape a ways ahead surrounded by other, less friendly shapes of various colors, Anna felt a simultaneous wave of relief and dread.

A sleek black cat was huddled by a now-empty sardine container, five other well-muscled cats looming over him. The black cat opened his mouth to hiss, revealing a mouth with several missing teeth. The other cats took a step forward threateningly, and Toothless swatted at them with a useless, declawed paw.

Anna wasn't sure what he had done to invoke their wrath. Maybe he had eaten the last of the anchovies and the band of alley cats were determined to make him pay. Or perhaps they were prepared to fight him for the last, unseen anchovy, and Toothless, as stubborn as his human, was not about to back down. Either way, if the alley cats lunged in for an attack, Hiccup was right—Toothless didn't stand a chance.

Anna bristled with rage at the thought of these bulky strays ganging up on someone half their size, bent on hurting him when they could just as easily chase him away. "Hey!" he shouted. "Leave him alone!" The cats ignored her, as most cats are bound to do when commanded to do anything by humans.

Anna let out a furious huff, and her eyes trailed down to her softball bat. She hadn't actually thought she would have occasion to use it, but here she was. Despite herself, she smirked. _So I never plan ahead, isn't that right, Elsa?_ she thought. _Well, later on you're going to hear all about who most definitely planned ahead_ this _time!_

Letting out her best war cry, Anna charged forward, bat braised and ready for combat. Still screeching, she swung wildly at the brawny cats (although not with the intention of actually hitting them, since Anna had what could only be described as a "hurt no living thing" life outlook, and yes, that applied to rude cats as well), being careful not to let the hefty bat get anywhere near Toothless. It took only a few swings for the mean cats to take off racing down the alleyway, yowling in terror.

Anna was relieved that Toothless himself did not complicate things by running away himself, and instead remained in his spot cowering by the wall. He gazed up at her, green eyes wide with terror, and Anna hastily dropped her bat and kicked it away.

"Hey Toothless," she said softly, sinking down into a squat to look less intimidating. "Wow, am I ever glad to see you…like, _really_ glad. Your human Hiccup's been worried sick about you, you know. Wait how happy he'll be that I found you!" The cat's ears perked up slightly at Hiccup's name, but he didn't move from his hunched spot by the wall.

"Uhhh…you want some tuna?" Anna jiggled the open tuna can around, and Toothless gave the air a couple of eager sniffs. She set it down on the ground and slowly backed away.

Toothless hesitated for a while, but finally slinked cautiously over to the can, giving it a few delicate sniffs before daintily beginning to nibble.

As Anna watched him, she wondered if she should creep up on him and snatch him up as he ate the tuna so she could carry him back to Hiccup's house. But the more she thought about it, the more carrying a squirming cat for 10 blocks didn't seem like a good idea.

Sighing, she pulled her phone out of her back pocket and found Hiccup in her contacts list (it was a miracle he was there at all—the only reason she even had his number was because she found it in a community message when they were texting with their group for the "History of the Cotton Gin" group project). Taking a shaky breath, she pressed the call button and held the phone up to her ear. She had never actually called him before, so the monotone rings on the other end left her a bit breathless. _Don't be awkward, don't be awkward…_

"Hello?" She started at the sound of his voice. She'd never heard it over the phone before, and somehow it made her heart beat even faster than it did in person.

"Uh…hey Hiccup," she mumbled. "It's Anna. I…ah…I found Toothless!"

"Really? You did?" She wasn't sure she had ever heard him so excited about something. He was typically calm and collected, the laugh he gave to accompany a snarky comment usually being the most intense emotion he displayed. But here he was, sounding like a kid who had just been informed he had twice as many birthday presents as he previously thought, and Anna liked him all the more for it.

"You bet I did!" she bragged, puffing out her chest. "It wasn't easy, but hey, with my great Girl Scout animal tracking skills, I managed!"

Anna heard him let out his breath. "Wow…thank you so much. He's still there with you, right?"

She glanced over at the black cat, still working on the tuna she had given him. "Yep. I was gonna pick him up and take him back to your house, but then I figured me trying to haul a cat struggling for freedom for 10 blocks might not be the best idea." She laughed nervously, and to her relief Hiccup laughed too.

"Okay, I can drive over and pick you both up. Where are you?"

"Behind Cally's Pizza."

Hiccup snorted. "Figures he would be after those damn anchovies. Word must've spread about them through the cat grapevine. Okay, I'll be there in a few minutes. Don't let him get away, all right?"

"Okay, I won't! See you in a bit."

"See you."

Hiccup hung up the phone, and the full weight of what was about to happen washed over Anna like a tsunami. Her crush—her beautiful nerdy Hiccup Haddock whom she had been admiring from afar and low-key stalking since she was 6 years old—was coming to pick her up in _his_ car (well, technically his dad's Ford Fiesta since Hiccup didn't have his own car yet, but close enough) and she was going to ride in _his_ front seat, just like she would if they were on an actual date. She let out a dreamy sigh and clutched her hands together in anticipation. This would easily be the most romantic moment of her life!

 _Oh no…_ Her stomach squirmed suddenly. _What if there's a horrible awkward silence the whole way?_ Anna pulled up safari on her phone and hastily googled "50 things to talk to your crush about."

In between trying to memorize the 50 questions, Anna stole glances at Toothless, still munching on his tuna. Cautiously she crept up behind him, making sure that he was fully preoccupied before slipping her phone back in her pocket and leaning down and lifting him up in her arms. He let out a grunt of disapproval, but Anna wasn't about to let him go exploring and be decidedly absent when her crush came to pick him up. Nothing would kill Hiccup Haddock's potential interest in her faster than her _losing_ his cat 5 minutes after she _found_ him.

"Sorry Toothless," she muttered, using one arm to hold on to the squirming cat and the other to pull out her phone again. Sinking down onto the pavement and leaning up against the back of the pizza parlor, she continued memorizing her list.

Trying to keep the fidgety cat still was not an easy feat, so Anna was beyond relieved when she glanced down the alley into the street and caught a flash of black Ford Fiesta driving by. She could only hope that it was headed for Cally's parking lot, and that it had the world's most attractive online gamer and dragon-obsessed nerd inside.

In a few minutes, Hiccup Haddock emerged from behind the side of the building in all of his baggy-clothed glory, the timid smile on his face turning into a full-on beam as soon as he saw the black cat.

"Toothless!" he exclaimed. The cat squirmed again, and this time Anna loosened her grip to allow him to go bounding over to his human. "Hey bud," Hiccup murmured, bending down and scratching behind Toothless's ears. The cat leaned into his touch, letting out a happy meow.

Hiccup looked up at Anna gratefully. "I really owe you one," he said sincerely.

Anna smiled as she met his beautiful green gaze, and it felt like he was finally seeing her for the first time. _That's all right Hiccup, you could just kiss me and I'd call it even,_ she wanted to say.

"No problem, it was my pleasure," she settled for saying instead.

Hiccup scooped up the sleek black cat, and Anna wasn't sure she had ever heard a cat purr louder. They skirted around the edge of Cally's Pizza and walked back to Hiccup's car, all the while Anna relaying her adventure of how she had found Toothless and rescued him from a nasty group of alley cats. To her delight, Hiccup seemed especially impressed with the part of the story concerning the softball bat, claiming he might not have thought to bring a potential weapon to scare off any tormentors. Anna's heart had never felt so light and fluttery, not even that one time when Hiccup had given her an extra (probably accidental, but still) chocolate kiss with her valentine in the 3rd grade.

As soon as they reached Hiccup's car, he turned to Anna and laughed nervously, giving her an apologetic smile. "Er…I kind of forgot to bring to cat carrier…would you mind holding on to him on the way home?"

"No, no, of course not!" she said quickly, although the mental image of Toothless desperately trying to escape her grasp while she simultaneously tried to make conversation with Hiccup was enough to make her cringe slightly.

He carefully slipped Toothless into her arms, and she traded him the softball bat and the now almost empty can of tuna, both of which he put in the back seat.

At first Toothless was just as agitated as Anna expected, pacing all over her and meowing anxiously as Hiccup turned on the car and pulled out of the parking lot. But by the time they reached the stoplight, he seemed to relax, and plopped down on Anna's lap. As they passed the alleyway, he even started purring.

Rush hour had just kicked in, and past the stoplight the traffic was backed up quite a ways. But as Anna admired the lanky brunette boy sitting beside her, she realized that she hardly minded. She looked down at the contented cat curled up on her lap, and suddenly all 50 topics of crush conversation seemed to fly right out the window in favor of one simple question.

"How did you get Toothless?" she asked.

Hiccup chuckled. "Ah, well, funny story. You see, for years and years I was begging my dad to let me get a puppy, and he was like, 'No son, we don't have room for a smelly, shedding beast in this house! Besides, it'll poop all over the nice back lawn I paid $50 to have manicured!" Anna giggled at his imitation.

"But I kept insisting, and saying I would clean up the doodoo and take him for walks and everything, and finally on my 10th birthday, my dad took me to the animal shelter…probably just to shut me up, but hey, I wasn't going to pick apart his motives." He smiled weakly. "So we were going to see the younger dogs, and we were walking through the cat room on the way. And I happened to glance in one of the cages and I saw this…this little black kitten. And he happened to look over at just that moment, and we locked eyes. He walked over to me, and he opened his mouth, and I saw that he was missing all these teeth…didn't seem to put a damper on his spirit, though. He started meowing at me, _right_ at me, so I stopped to look at him and my dad got all frustrated like 'Son, what are you doing, we came here for a dog!'" He rolled his eyes good-naturedly, and Anna laughed again.

"Well, I ignored him, and asked the caretaker we were with about the kitten. He said that he could never put him into the playroom because the other cats would always pick on him. And no one wanted to adopt him, either…probably due to his messy teeth. Or maybe that whole black-cats-are-bad-luck thing. In any case, I think I realized in that moment why we had connected. We were…we were practically the same. He knew what I had been through. Being laughed at, feeling unwanted."

Anna reached out and touched Hiccup's arm comfortingly. She knew all too well the torment he had endured in elementary and middle school, always being sneered at for reading books and play trading card games instead of playing sports like the other boys. She had always wanted so badly to stand up for him, but she had never found the courage to…never found the courage to call that much attention to herself. Never wanted to risk the bullies turning their attention to her and picking her apart right in front of Hiccup.

"And the longer he looked up at me with those big innocent green eyes of his and aimed his squeaky little meow at me, the more sold I was on him," Hiccup finished. "I completely forgot about any puppy I might have wanted."

"I'll bet your dad was relieved," Anna joked. "Cats are so much less work! Don't have to train them or take them on walks or anything."

Hiccup snorted. "Excuse me, have you _met_ my dad? He _hates_ cats with a burning passion. Nah, it took five times as much convincing to get him to buy me a cat than it would have for any dog, even some puppy who chewed up literally everything."

"Well, I guess it worked, huh?" Anna said, scratching under Toothless's chin. The black cat tilted his head back, purring louder.

"Sometimes I still wonder how it did," Hiccup admitted.

"You're lucky, you know," she sighed, still running her fingers through Toothless's thick, black fur. "I've always wanted a dog. Or…or a cat. Either would be fine, really. But of course my parents never wanted to put in the work, and they didn't trust _me_ to. No, they thought I would just dump the whole job on Elsa because _she's_ the responsible one." Anna snorted in annoyance and rolled her eyes. "And of course Elsa didn't even want a pet, so she wasn't going to push the whole thing! So…uh…that's the story of how I grew up petless and sad. _But!_ " Her eyes lit up suddenly, and she shot Hiccup a mischievous glance.

"As soon as I graduate from college and get my own apartment-thing, I'm gonna buy _two whole dogs_ , all for myself! And ah…maybe I'll get a black cat too…you know…to help solve the whole bad luck anti-adoption issue?" She searched his face hopefully for some kind of approval, which he gave to her in the form of a small nod.

"That's good of you. The black cats out there will thank you for it."

"I think I want one of my dogs to be a big white dog," she went on excitedly. "A Samoyed! He'll be big and fluffy and really nice and I'll name him Olaf. And my cat…hmmm…maybe I'll get a girl black cat and name her Inkblot. Is that…uh…is that too cliché?"

"Well, I mean…I named my toothless cat Toothless, so you can't really get much more cliché than that." At this, Toothless let out a contented mewl and leaned over to Anna's outstretched hand, rubbed his head up against it.

"You know, he really seems to like you," Hiccup chuckled.

Anna looked down at the cat fondly. "I mean, considering I was swinging a softball bat at him 10 minutes ago, that's actually a huge relief. Not that I was swinging it _at_ him," she clarified quickly, seeing the alarmed look on Hiccup's face. "Like, I was swinging it in his general direction while trying to scare other cats off, so I was actually trying to help him and whatnot, but he wouldn't know that since he's a cat, but I hope he did kind of know I wasn't swinging at him and I guess he did, since he seems all right with me now, or maybe he's already forgotten the whole thing. Sorry, am I rambling?"

"Believe me, I've heard worse," Hiccup said with a smirk. "Toothless is a smart cat. I think he probably _did_ know on some level that you wanted to protect him. I think he's got a lot better understanding of what's going on around him than he lets on. Don't ask me how, though."

"Cats are funny that way," Anna replied. "You know I read that there was a study that said they can understand most of what we're saying to them, and they just don't care? Because I can totally see that!"

At this point, they were pulling into Hiccup's driveway. Toothless put his paws on the window ledge and eagerly looked out into the front lawn. After he stopped the car, Hiccup grabbed the softball bat and tuna can from the backseat and walked around the edge of the car, opening Anna's door for her (a chivalrous gesture she appreciated, although she was no doubt a strong, independent woman who could open her own car doors. Although maybe not in this case, considering she had a cat on her). He lifted Toothless off of her, slinging the cat's front paws over his shoulder and resting his hand under his rump.

"Any way you'd be willing to give that tuna up?" Hiccup asked. "I think Toothless might like to finish it off."

"Sure, here!" Anna quickly dropped the open can into his outstretched hand, relieved that she wouldn't have to think of a way to dispose of it that didn't involve her parents asking why she, someone who couldn't stand tuna, had forced down half of a perfectly good can and tossed the other half out.

She walked him to his front door and opened it for him so that he could release Toothless into the front room. The cat scampered off to the kitchen, and Hiccup slammed the door shut before he could change his mind.

"So…thanks again," he started awkwardly. Anna laughed nervously.

"You're…uh…you're welcome! I still can't believe I actually ended up using that animal-tracking stuff in real life. Like…what?"

Hiccup smirked. "Yeah, we city-slickers can barely find our way around town without Siri, let alone hunt down a bear in the forest. With the exception of Girl Scouts, of course, and their impressive bear-finding skills—which clearly translate to other animals as well."

"But the real question is, do I _want_ to find a bear?" she laughed. "I mean, ya know, if I wanted to get eaten that day, then sure. You know how you're just in the mood to get eaten alive sometimes? Ah, sorry…that wasn't very funny…" Anna looked away, tucking a loose strand of hair behind her ear.

Hiccup didn't say anything, but gave her a soft smile. Anna felt her cheeks reddening and her entire body starting to burn. _Oh god, he's looking at me, he's looking at me! Geez, he's never looked at me this long before…what do I do? Do I panic yet? Should I run before there's an uncomfortable silence and he starts hating me for being a socially awkward loser?_

"You know, it's funny," he said finally. "I've lived on the same street as you since we were kids, but all this time I've never really _known_ you."

"I know," Anna said sadly.

"I kinda feel like I missed out."

He stated it like an analytical fact, a casual statement detached from the flirty implication that would usually have been present. But even with the logical tone to it, it was still enough to make Anna's entire world spin. Did he really think that highly of her?

And then, at that particular moment, and idea occurred to Anna which might well have been the riskiest and stupidest idea that had ever graced her mind.

Rapunzel had always been a large proponent of the "seize the moment" philosophy, always being the one pushing Anna toward Hiccup whenever he was sitting alone at lunch or casually pulling books from his locker undisturbed by friends, whispering "It's now or never!" in her ear. Anna was always the one holding back, grinding her feet into the floor and protesting in a panic, insisting vehemently that now was not a good time to woo him and she would have other chances and how would she start a conversation anyway? No, they both should just move right along and maintain the safe status quo.

So Anna was sure Rapunzel would be proud of the utterly blockheaded thing she was about to do.

"Doyouwannagoseeamovie?" Anna burst out. "Like…on Friday or Saturday or something? We could go see that one that's like _Revenge of the Ancient Dragon Masters_ or something like that. I just know that you like dragons because I saw you drawing them in math class the other day…I swear I wasn't watching you or anything! I sort of just happened to glance over and see them…oh my god, please don't think I'm creepy!"

Anna covered her face and looked away. _Stupid, stupid, stupid!_ She had been so close to getting a date with the dreamboat that was Hiccup Haddock, and she had gone and screwed the whole thing by letting it slip that she had been looking at him in math. Now he was definitely going to put the pieces together right away and figure out that she always stared at him in math class and he was going to decide that she was a total creeper and a horrible person and a stalker and definitely _not_ the sort he wanted to go see _Revenge of the Ancient Dragon Masters_ with.

"Sure."

"Wait…what?" Anna peeked at Hiccup through her fingers. He didn't look particularly disturbed, although he did look a little amused.

"I'd love to go see _Revenge of the Ancient Dragon Masters_ with you. I've really been wanting to see it, actually."

"So you…okay, great! So, um…does Friday work for you?"

"Sure, no problem."

"I guess I'll find the movie times later and I'll text you about it?"

"Sounds good to me."

"Okay, um…I'm going to go back to my house now."

"All right, see you Friday! Or whenever."

Anna waved awkwardly at him as she scurried away, making her way down his front path and across the street. As soon as he was out of earshot, she burst into a series of excited giggles. She had a date with Hiccup Haddock! All she had wanted was a reason to talk to him, and here she was with a slot in the not-so-distant future of hours upon hours to do just that, and maybe, if she was feeling ballsy enough, to kiss him.

Anna pulled out her phone and quickly began dialing Rapunzel's number, already impatient to tell the story of how a single missing cat had led to her finally winning over her crush of 10 years. It was almost too good to be really happening, but Anna was hardly going to complain about the insensibleness of it all.

She turned and shot one last smile at Hiccup's house, and the black cat perched in the front window. _Thanks, Toothless!_

* * *

 **Hey suckers, I am BACK, with more Hiccanna as promised! This time in the form of what I hope is an adorable modern AU. Funny thing is that I'm usually not super into Big Four modern AUs because, to be honest, I find them a bit boring if they're not done well. (I mean, we're taking an archery badass, a girl with magic glowing hair, a guy who has a pet dragon, and a winter spirit, and turning them into…normal high school students?) BUT I saw the CUTEST picture of Modern!Hiccup with Toothless as a cat, and me being the Hiccanna-loving nerd that I am, the brain instantly formed the idea of a modern AU where Toothless goes missing and Anna, having a crush on Hiccup, goes out to find Toothless to impress him. Took a while to generate enough believable storyline around this little prompt to make it into an actual story, but here we are! So enjoy this fun and hopefully kind of funny cat-finding adventure in which Sue and Cally are most definitely based off of older versions of myself XD**

 **Quick disclaimer: Never having been a Girl Scout camp myself, I actually have no idea whether or not animal-tracking or anything of the sort is taught at Girl Scout camp ^^; Don't get on my case if it's not (which it probably isn't)! Just pretend that this is a weird subsect of Girl Scout camp where they teach animal-tracking. OR that this is a weird AU where teaching animal-tracking at Girl Scout camp is a regular thing. In any case, the animal-tracking stuff in here is all from a real animal-tracking website, so it's actually authentic! In case you ever want to try it out in the forest XD**

 **And so continues the slow rise of Hiccanna out of obscurity, one fanfic at a time! Two down, many more to come!**


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